


My Eyes Adored You

by prophetkieren



Category: Supernatural
Genre: AU, Alternate Universe, Destiel - Freeform, Fluff, funny spin on things
Language: English
Status: In-Progress
Published: 2015-03-03
Updated: 2015-03-12
Packaged: 2018-03-16 03:51:02
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 8,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3473363
Author URL: https://archiveofourown.org/users/prophetkieren/pseuds/prophetkieren
Summary: <blockquote class="userstuff">
              <p>The story of a reunion years in the making.<br/>After a fight, Cas and Dean haven't spoken in years until Cas moves to a new city with his best friend and runs into Dean.<br/>Now their shenanigans unfold and drag everyone around them into it.</p><p> </p><p>Pretty much a lighthearted AU with lots of tomfoolery and fun times among four friends.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> So basically, this is all in good fun and hopefully it's enjoyable to you.  
> I feel like this is pretty likable, but what do I know.

"Can you please, for the love of god, shut up for once?!" Castiel shouts at his insistent, blue haired friend.

  
"But Casssyyyyy, I know we go this way! Just trust my instincts for once!" She slurs her words as she stumble over her own feet.

  
"Sydney, no offense, but you don't even know where your own hands are. I mean, how could I possibly trust your instincts when you're three times over the legal limit for alcohol consumption..?" Castiel looks around the shady neighborhood as he pulls Sydney closer to him. "Just. Stay close. You've taken us into the ghetto and I don't want to have to encounter large thugs while you're drunk."

  
Sydney hiccups before protesting Castiel's assumptions. "Cassy, I s-swear to you that I-I-I am not drunk-k. I'm juuuust having some f-fun. Lay off, ma-an. There aren't any lar-rge thugs 'round here. Maybe just some angry biker du-udes, but none of them 'thugs'."

  
Castiel notices a dark figure in the distance. "Sydney. I think we should just turn around and run. Like run and not question any of this later." The dark figure gets closer and closer while Sydney still refuses to take Castiel's suggestions seriously. As the figure nears, Castiel can feel his heart thumping away in his chest in fear he might be pummeled into a bloody pulp.

  
The figure comes close enough into view that they can make out his clothing; leather and denim. "Oh god, Sydney he's a biker." Castiel turns to run but realizes Sydney is still standing there with a death grip on his wrist. Castiel tries to shake free of her hold, but she only tightens her grasp. "Sydney, I love you and all, but if you want to stand here and get killed more power to you, just keep me out of it."

  
Sydney shushes Castiel and pulls him toward the figure. Only then could they make out his facial features. Eyes greener than any Emerald found in Colombia. Freckles that danced across his cheeks and down the bridge of his nose. Hair that resembled chocolate Mousse, in color and in style. Castiel looks over him once more, taking in his appearance. The man was donned in a light green button up shirt, light denim jeans, and a brown leather jacket that was slightly large on his body. Castiel realizes that this face is all too familiar, but he's certain he's never met this man since they just moved here.

  
Sydney stumbles forward, nearly into the man. "-'scuse me, mister. Can you-ou help me and m-y friend out here. We seem to be lo-ost and we just moved here and 69th Avenue and Fangboner Road seem to n-ot exist and I'm sure you wouldn't let my lo-nesome self and my pre-e-etty friend be left vulner-a-able." The man looks from Sydney to Castiel, he contemplates it and decides it won't kill him to give them directions; and she was right, her friend was pretty.

  
"Um, yeah, sure. You said you're going to 69th and Fangboner , correct?" Castiel nods. "Well, you guys are headed in the wrong direction...you're going to need to go down Main Street and then South Washington Street...Actually, I'm sort of heading that direction, so I can escort you two home." He looks at Sydney with a concerned look, then makes eye contact with Castiel who feels his cheeks grow hotter at that second. "I'm sure you're going to need a hand helping her home. Don't worry, I'm not going to try anything funny to either of you. I'm Dean by the way." Dean extends his hand to Castiel, whose cheeks are on fire by this point.

  
"Dean?" Castiel repeats and Dean nods. "Hm. I'm Castiel and this is my very drunk friend, Sydney." Dean's cheeks turn candy apple red and his eyes gross in disbelief. He shakes his head and mouths 'no' repeatedly. Castiel just stares at Dean trying to figure out what's going on in his mind. "Is something wrong?"

  
"Castiel?! Oh my god! I can't believe it's actually you!" Castiel still stares at him confused. "Cas, it's me, Dean Winchester. Remember that time you stood your ground when little Sammy was getting pushed around?" Dean laughs. "You ended up with a black eye and I never got the chance to thank you for helping my little brother out...Is this the Sydney? Your sister, or rather best friend? Gosh, you guys are still hanging out. Some things never change."

It dawns on Castiel that he's talking to his high school crush. Mr. Captain of the Football Team, the school bad boy who secretly had a soft side to him, easily the biggest womanizer Castiel has ever known and yet somehow he couldn't draw his attraction away. "Dean. It's been so long, I'm surprised you actually remembered us." Cas feels his heart race when he thinks about how his crush remembered him this long.

  
Sydney cuts into the conversation, slurring her words a little less this time. "Okay, lover boys. Who's going to get mama to bed because she needs her beauty sleep." Sydney laughs to herself.

 

 

After a few confusing turns, they find themselves at the front door to an apartment building. Dean looks up at the towering building. "Here, let me help you get her up the front steps and to your door." Dean helps Castiel lug Sydney up the stairs and through the front door, laughing when she starts passing out and almost falls flat on her face. He throws her over his shoulder as Castiel smirks at her drunkenness.

  
They step off the elevator and Castiel searches through his pockets trying to find the house key. When he does, he unlocks the door and swings it open so Dean can carry Sydney through the doorway. "You can just put her in her bed." Dean opens the first door he comes across. Castiel hurriedly closes the door in Dean's face. "No! That's my room! It's the next door." Dean lays Sydney down in her bed and Castiel tucks her in before they leave her sleep it off while those words linger in his mind.

  
Dean stops in the living room and turns to Castiel. "She's going to have a killer hangover tomorrow." Dean laughs as Castiel passes him to the kitchen. "Does she always do this? I know she always smuggled alcohol into school, but I didn't know she'd actually get this hammered."

  
Castiel huffs. "This isn't even her worst. She'll just power through that hangover like it's a papercut. I'm surprised she even passed out. Anyway, would you like a drink?" Castiel looks through the little window that leads to the living room and Dean nods. "It's just ordinary beer, I hope that's fine. It's all she lives on anymore." Castiel hands Dean the beer as he sits beside him on the couch.

  
Dean takes a swig of beer. "You know, this is a really pretty place." Castiel nods in agreeance. "So, why did you nearly break my neck when I opened your bedroom door? Got some hidden secret in there? A dead body maybe?" Dean laughs nervously and Castiel stays silent. "Oh god, there's not a dead body in your room is there? I'd expect that out of Sy-"

  
Castiel cuts him off before he can finish his sentence. "No, there isn't a body in there. But you still can't see what it is." Dean gives him puppy dog eyes, the one thing that never failed to work on anyone Dean had ever known. "Sorry, Dean. I'm not going to fall for your puppy dog eyes. That trick won't work on me."

  
They hear a crash that startles them both. Dean stands up like he's ready for a fight. Castiel notices his defensive stance. He stands and puts his hand on Dean's shoulder. "Dean, it's nothing to worry about. I know what caused it." Dean starts down the hallway. Castiel grab his hand to stop him, but Dean just keeps going. "Dean, please. Don't open the door." Dean opens Cas' door and a hellacious dog jumps on Dean causing him to knock down Cas. Dean quickly gets up, giving Cas a hand. The large, white dog barks at them. Cas expeditiously opens his bedroom door. Shoving Dean in, he closes the door on the dog.

  
Dean turns around to face Cas. "Cas, what the hell was that?" Dean puts his hand on his hip. "A huge glacier just smashed into me, I feel like the Titanic right now." Cas laughs to himself as he turns on the light.

  
"I believe that's called a dog. Amusingly enough, his name _is_ Glacier." Cas laughs again and Dean just stares at him completely dumbfounded. "Trust me, he's nothing to worry about. He's just a big klutz that knocks everything over and barks at it like someone's chasing him." Cas notices a broken vase by the bed. "Well, that's what broke; my vase." Cas picks up the flowers with a sad look on his face. "I don't have anything to put them in, now they're going to die and they're just so beautiful." Cas goes to open the door when Dean stops him.

  
"You think it's a good idea to go out there while that monster is parading around? You must have a death wish." Cas chuckles and opens the door. Glacier is laying in front of the door with a pitiful look on his face. Cas gives Dean a 'what did I tell you' look. "He's just going to rip your throat out when you're sleeping."

  
"Yeah, I can see that happening. He's just so ferocious." Cas laughs as he steps over Glacier. Dean stares down at the fluffy, white dog. "I'm going to just go find something to put these in." He holds up the flowers as he enters the kitchen.

  
"I know what you're up to. Your cute face won't convince me otherwise." Glacier sits up and wags his tail. "Oh no you don't. I'm not falling for that." Dean hops over him and darts to the kitchen where he finds Cas rummaging through the cabinets. "Have you found something to put your flowers in?" Cas turns and shakes his head. Dean nods and goes to the living room. He returns with his beer bottle and dumps the remaining alcohol down the kitchen sink before rinsing it out. He turns to Cas, holding out the bottle. "Here, this will work. It'll even keep them perkier longer...kinda like my breasts"

  
Cas laughs and takes the bottle. "That's really cute and creative, actually. Thank you, Dean." Dean nods. Cas smiles down at the bottle before walking back to the bedroom with Dean trailing behind. He places the flowers on the nightstand and chuckles. "Remember when you threw that tater tot and it hit Christie Mathis and her parents threatened to sue?"

  
Dean laughs as he sits on the bed. "I know. Or that time I got caught in the supply closet with Sara Richards and her dad tried to shoot me?" He laughs again until he realizes Cas didn't find that one funny. "Anyway, Cas, how have things been for you guys lately? I mean, we had that argument and then after graduation, I had no way to contact you." He looks up at Cas who shrugs.

  
"I don't know. I guess you could say things have been hectic...but...I came out to Uncle Metty." This catches Dean's attention.

  
"Oh yeah? How'd that go?" Cas sighs. "I take that as a bad." Dean pats the bed next to him. "Why don't you sit down and we can talk about it? I know you're really close, or at least you guys were..." Cas sits next to him.

  
"Well, he was talking about introducing me to this girl he thought I would be interested in. I kept dropping hints that I just wasn't interested. So, I just straight out told him I'm gay and don't wish to be involved with any girls." Cas looks down and Dean puts his hand on his shoulder. "Do you mind if I put some music on? The air is a bit thick in here." Cas' attempts to make things less awkward isn't working.

  
"No, go ahead." Cas nods before standing. He opens the cabinet and flips through various records before deciding on one. "Is that...a record...?" Cas smirks and nods.

"Sure is." He opens his record player and puts the record on. Lowering the needle into place, he turns to Dean. "It's one of my favorite songs, December, 1963 by The Four Seasons. Frankie Valli just has the loveliest voice I've ever heard." Dean stares at Cas with a confused look on his face.

  
"They still make records and record players..?" Cas laughs as Dean just tries piecing this information together. He can't comprehend how records are still around in 2015. "Wasn't that like a pre-60's thing?"

  
"Yes, they still make records and record players as you can see. This one's pretty old though, but they do make modern versions. I just like the old stuff, you know?" Dean nods. "Okay, I'll finish now. After I told him, he thought the only logical thing to do was to, as he said, beat the gay out of me."

  
Dean shakes his head. "He didn't. Tell me he didn't, Cas." Cas lowers his head. "Fucking shit. Cas, I'm sorry. If I see him again, I'll break every bone in his body." Cas smiles up at Dean.

  
"No Dean, don't apologize. It's not your fault. It's better to just cut his negativity out of my life entirely. It's kind of the reason why Sydney and I moved out here in the first place. We probably never would've left Maine if it hadn't been for that incident. If we hadn't left, you and I never would have met up again and what fun would that be?" Cas feels his cheeks getting hot for the thousandth time since he's been near Dean.

  
Dean nods. "You're right. The reason you came here is shitty, but at least you know someone here." Dean catches himself blushing. "Anyway, there's something I've been meaning to tell you. After the argument and everything, there was never an appropriate time." Cas feels his heart rate increase rapidly. What could Dean possibly want to say that he hasn't already? "The truth is, the reason I was acting so selfishly and acting like a complete moron was..." Dean takes a deep breath."..because I was, and kinda still am, head over heels for you."

  
Dean looks over to see Cas' reaction. Cas' mouth is wide open and his face is completely flushed red. His heart is beyond beating out of his chest. Did Dean really just say that? The Dean Winchester just admitted that he had, and still has feelings for Castiel Parker? But how could that be possible when Dean's always been a womanizer?

  
“Uh - I – Wh – Look at the time! It's nearly two am! I have to get to bed. I'm sorry, Dean, but can we talk some other time?” Cas quickly stands up, Dean mimicking his actions. “I wouldn't do this unless it was absolutely necessary, but I truly need to get up early, tomorrow.” Cas leads him back through the apartment and to the front door.

  
“Oh no, I totally get it. We can talk some other time. Hopefully soon, I've missed talking to you about everything.” Cas can feel a lump in his throat which he assumes is his heart.

  
Dean turns to Castiel and smiles. "You know, this was really fun. Reminiscing, getting an earful of your music taste, helping you escort your drunken lady friend home. We should do this again, soon." Dean gives Cas a hug and Cas can feel his cheeks getting warm. "See you."

  
Cas smiles. "Bye, Dean." Dean steps on the elevator and with a final wave, the doors close. Cas can't help but smile. He heads back to the apartment and climbs into bed. He lets out a content sigh. "Wow. Sydney missed so much. I have to tell her it all." He rolls over and looks at the makeshift beer bottle vase sitting on his nightstand. There's no doubt he'll forget this night.

 

 


	2. Vertigo

**Summary for the Chapter:**

> Sydney and Cas have a dispute.  
> Sam encounters a drunken prostitute zombie.  
> Sam discovers Dean's 'secret'.  
> Then Sydney treats Cas to some shopping.

 

"Sydney. You know relationships do stem from everything other than sex, right?" Cas shifts in his seat. "Like getting to know the person before having sex with them. Cherishing the moments you spend with them, the moments that don't come everyday. Just laying with them in bed and talking about your day while holding their hand." Sydney cackles.

"You're only saying that because you're still a virgin and haven't had a dick up your ass yet and once you do, you'll definitely change your opinions on what relationships revolve around." Sydney smirks to herself. Cas sighs.

"You know, of all people I wouldn't think you'd be the one to mock me for saving my virginity for the right guy. I'm sorry that I didn't just throw mine to the first guy to pay attention to me like you did. Maybe you've never had an actual boyfriend because you're so quick to get in his pants." Cas walks to the door before stopping. "Guys aren't going to want to marry a woman who's already slept with half of his friends and relatives. They're not even going to think about a second date if you spread your legs on the first one. It's sad to say, but you really need to check back into reality before it's too late.”

She's taken aback by his words. “Cas, why-” He cuts her off mid sentence by putting his hand up.

“It had to be said sooner or later, and better sooner rather than later. Especially from me instead of some itinerant person.” He stands up and puts his jacket on. “Please, get some help or something.” He walks out, closing the door behind him leaving her to dwell on his last words. She gets up and grabs a glass and pours some whiskey in it.

 

* * *

 

Meanwhile, across town Sam is humming a tune as he strolls along. There was nothing he enjoyed more than watching his dogs fumble around in the cool autumn breeze, except probably someone to share that feeling with. As he was lost in his thoughts one of the dogs found her way down into a ditch causing Sam's heart to jump out of his chest.

“Luci! Luci!” He peeks over the edge to find her perfectly okay. “Why did you need to-” He lets out a yelp of his own. “Is that a dead body?” Sam says to himself as he hops down into the ditch to grab his dog. He contemplates on whether or not he wants to get involved in this mess. He picks up Luci and looks over the mysterious woman laying face down with a heel cocked in the air and a whiskey bottle in hand. _Classy_ he thinks to himself, sighing because he knows if he leaves her here, there's a chance someone might see him and assume he's the killer and he'll have to explain why he left her body there without calling the cops. He looks around to see if there's anyone else nearby that he can dump this on. Much to his avail, there isn't a soul in site. Just then he hears a low grumble as a hand grips his ankle. He lets out a shriek he wouldn't like to admit came from his mouth.

 _“SOMEONE HELP THERE'S A ZOMBIE!”_ He screams at the top of his lungs as he attempts to pull away from the death grip. Then it dawns on him, there's no way a zombie could be _that_ strong. He looks down at the woman holding onto his ankle. “Hey, ma'am..?”

“I ain't no man! I gots these here titties! Respect the titties, man.” Sam thinks for a moment, confused as to what she's talking about. His thoughts are stopped by her tugging on his pants, trying to get up just to fall back to her knees. He bends down and helps her to her feet, keeping a grip on her arm to keep her on her feet. “Hey, trusty stead, wanna take this queen back to her kingdom?” She pokes his chest and he gets a whiff of her alcohol stained breath.

“Uh, yeah, sure, where's your kingdom exactly..?” He looks her over once more to try figuring out what kind of human gets hammered and passes out in a ditch dressed in revealing clothes. Then he realizes there's only one kind of person who would ever be caught doing that: _a prostitute._ It all starts making sense to him now.

“Go-a th-this way.” She points him in the right direction, or so he hopes. Sam's not sure if he's supposed to make small talk or not, so he keeps his mouth shut and lets his mind wonder about this drunken lady trying to create scenarios that led her to this. _Maybe she's a successful CEO and just got a promotion so she went out to party with some friends last night and this is where she slept._ That one didn't seem very likely to him. _Perhaps she had a tough breakup and tried to cover the hurt with alcohol and on a drunken voyage home she stumble into this hole._ That one didn't seem likely either, the only one that seemed likely was the one where she was a prostitute and was leading him to her pimp and he'd have to explain this to a large, frightening man with a goatee and a cigar dangling from his mouth.

“Hey, hey. This is it! Right here, trusty stead. Woo-hoo! Mama's home!” Sam looks at the building. _It didn't_ _look like a place where a pimp would live...unless that pimp wanted to stay under_ _the radar._ He realizes this place looks all too familiar to him. He takes her up the stairs to apartment 4C and knocks on the door. Anxiously waiting for an answer from someone who isn't going to wrap their hands around his throat and squeeze until the life drains from his eyes.

 

* * *

  
At that moment, Cas and Dean were cuddled up on the couch in Cas' apartment as they marathoned all the movies Cas owned. It was Dean's idea, they'd strip down to nothing but their underwear, order some take-out, and watch movies until they fell asleep in each other's arms. Well, that part he hadn't told Cas, he was just hoping that bit would happen.

There's a knock on the door and Dean hops up walking over to the door as Cas pauses the movie. “Quickest Chinese del-” He stops dead in his tracks as he stares at his younger brother standing outside the door.

“Dean, what's wrong?” Cas stands and looks at the unexpected guest at the door who most certainly wasn't there delivering their order of white rice and steamed dumplings, but instead to deliver an entirely inebriated blue haired prostitute better known to them as Sydney. “Wh-who's this? Do you know him..?” Cas awkwardly asks as nobody else was going to say anything to explain the current situation at hand.

Dean swallows. “Yeah, _Cas_ , remember little Sammy? This is not-so-little-Sammy.” Cas can feel his good mood sprint across the room into the dark corner because he knows Sam has no idea that Dean hasn't been sneaking away to hook up with a busty blonde. He knows Dean would never have told Sam he was into guys because he didn't want his little brother to think of him in any other way that didn't include the words 'awesome' and 'my role model'.

“S-Sam, it's so nice to see you after all these years! You've definietly had a late growth spurt..” He attempts to make small talk, hoping it'll distract him from the fact that they're both standing there in nothing but their underwear. Sam just looked back and forth between the two of them with no expression for them to read until he finally opened his mouth.

“Is there something you want to tell me about, Dean?” He asks, eyebrows raised.

Dean laughs. “No, I don't have anything to tell you..” He tries to avoid making eye contact with Sam.

“Are you sure, Dean, it kinda seems like theres something that you've been hiding from me for quite some time. I'm your brother, you know that I'll stick by you no matter what you choose to be even if that includes this current lifestyle that you've chosen..” Dean's standing there with his mouth agape, with Cas wide-eyed behind him.

“W-what're you talking about, Sammy?” He tries playing smooth, hoping Sam can't see through his shield.

“Dean..I had no idea you were, uh..” He lets out a deep breath. “I wish this wasn't the case, but since you're, you know.” He pauses trying to find the right words, scratching his head ignoring the fact that Dean is about to pass out at any moment. “Well, I guess I should put it out right, I never would've guessed that you would be a pimp!” At the sound the sound of those words, Dean's face scrunches up into a scowl.

“A what?!” He shouts at his younger, but definietly taller brother. “Why would you think I'm a pimp?!”

“Well, why else would you know her?” He looks to Sydney who's trying to take another sip from the bottle in her hand while examining her broken heel in the other hand. Dean rubs his temples trying to keep from blowing his top off.

“Sam, that's Sydney. You know the girl who bullied you in high school? This is Cas, her brother. You know the one who got a black eye from her for helping you out?” Sam lets out an inaudible sound before shoving her into them.

“Why didn't you tell me that sooner?! How could you let me stand here with her dangling on me like that?! Have you forgotten she made high school a living hell for me?!” He shakes his head. “Now I wish you were a pimp.” He turns and heads down the way he came before.

Dean turns to Cas with a confused look on his face. “Do you think he, y'know.” He walks Sydney over to the chair. “Do you think Sammy knows, about us?” Cas looks at him as he tries to string together some words.

“Well, considering the fact that he assumed you were a pimp and completely ignored our clothing choice, I think it's safe to say that he hasn't the _slightest_ clue.” Cas gives him a reassuring smile.

 

* * *

 

 

The Next Day

 

Sydney wakes up early and finds Cas sitting at the kitchen table drinking a cup of tea and doing the morning crossword. She sits down across from him, they sit in silence for awhile before she speaks up.

"Um.." He looks up from his crossword puzzle. "Apathy." He cocks his head to the side. "Another word for the absence or suppression of passion, emotion, or excitement. Thirteen down." He looks down at the puzzle and fills in the squares. "So, I wanted to say a certain word that doesn't exist in my dictionary and so, I thought of something to do for you instead. We're going to the mall and I'll treat you all day." Cas looks at her for a moment. 

"Wouldn't you rather just say sorry rather than spend your money?" He looks at her questioning what her true motivations are. 

"Actually, no, I would not. It's Mr. C's money, so we're all good." She smiles at him and he just sighs.

"Well, fair enough, I guess I can go get a new cardigan.." He stands. "We might as well go now before Dean comes over." She leaps out of her chair dragging Cas to the car and speeds off to the mall. 

Cas attempts to walk peacefully, but that idea is completely crushed when Sydney grabs his arm and forces him to walk faster. 

"Here!" She yells to him. He looks at the store she stopped in front of. Peek-A-Boob. Cas looks at her, now realizing her true intentions. She struts in and spots an employee. "Excuse me, could you measure my friend's breasts?" She walks over and pulls Cas into the store. The woman looks at them confused for a moment. "He's getting a sex change and he's not sure what size would suit him, so I figure why not measure what he's got now and work from there?" Cas grumbles and rolls his eyes, figuring he might as well go along with it since he said some awful things to her and knowing she could do far worse. He puts his arms out to the side so she can slip the measuring tape up and around him, she counts the numbers, then re-adjusts it and counts again. 

"Okay, dear. You're a 32 AAA. I think a large B would look just fine on you." She smiles and walks away. Cas gives Sydney a look. 

"Hey, it needed to be done because we're going to pick out some cute lingerie and slut you up for Dean." Cas sighs for probably the hundredth time that day as he follows her through the store grabbing nearly everything she sees. "Hurry up, I want you to wear one of these when Dean comes over later." She opens a door to the dressing room and shoves him in following behind, pulling his shirt over his head.

"Hey, wait a minute. Why are you in here?" 

"Well, I'm going to judge what you look like. Unless you would rather I go out there and you can come out and model it for everyone in the store." He pouts.

"Okay, fine give me one." He gets undressed and she hands him a lavender lace thong to try on. He puts it on and looks in the mirror. "Oh dear heavens. These are just not going to work for me, Sydney." He quickly pulls them off as she hands him a crotchless pair of panties, he sighs and throws them on the floor. "That's **not** happening, no." She hands him a pair of light blue and pink lace panties with little flowers on them. He puts them on. "Now these, these are really cute. I want them." She hands him a pair of translucent peach panties with big bows on the side, he puts them on. "Aww, I look so cute! These are a definite." She hands him the final pair, a yellow lacy pair with a ruffly skirt and he puts them on. "Wow, I think Dean will enjoy these." He puts his clothes back on and they exit the dressing room with the underwear in hand. She grabs him some lace thigh highs and garters to accompany his new panties. 

"I have something to tell you. There's this guy." He looks at her with eyes filled with curiosity and a smile plastered on his face. "I met him recently and he's pretty cute and he loves dogs. Oh, and he has this beautiful long hair that he tucks behind his ears and it's so adorable. He's tall and gorgeous, he's so manly and yet so gentle. He's the outdoorsy type and he's a health nut. He wants to go out and I said yes, and I'm so excited. He's so perfect." Cas thinks for a moment about the man she just described.

"Woah, wait a second!" His tone gets serious. "Do you realize who you're going out with?" She shakes her head. "I didn't think so, you were far too wasted when he came over. You're going out with Sam."

"You know his name?" He sighs. 

"Yes, I know his name because that's  _Sam._ You know, Dean's younger brother. The one you tormented for two years and whose life you made hell. I don't know how you could forget, but you gave me a black eye for defending him. That Sam." She looks down in confusion. _How could she not have realized that after she harassed him for years and why would he ever want to take her out?_

 

**Notes for the Chapter:**

> Sam's dogs don't disappear, they just follow him.


	3. The Devil In Disguise

**Summary for the Chapter:**

> The gang finds suitable group costumes.  
> Halloween night, they head to the woods to dick around after Sam suggests it.  
> They find out there's more to the woods than they thought.  
> Dean finds out just what gets under Sydney's skin.  
> Sam questions himself about his attraction to Sydney when he realizes she's a complete mess of personality.

“CASSSSS!!!” Sydney shrieks as bursts open the door to his bedroom. “Cas! Cas! It's less than a week until Halloweeeeen!!!” She jumps onto the bed, shimmying in-between Cas and Dean. She presses her back into Dean and her bosom against Cas' back. “Casss!! Halloweeen!” She pinches his ear, waking him. He rolls over and squints at her.

  
“What are you doing in here? You're not Dean..” He rubs the sleep out of his eyes and yawns. “What time is it, anyway?” He stares out the window, noticing the sun isn't out yet. It couldn't be _that_ early.

  
From the other side of the mountains Cas hears a lonely call. “It's five in the morning..” Cas lets out a sigh.

  
“Cas, we have to get going! We need to go and get our costumes!” She eagerly bounces around in the bed causing both men to groan.

  
“Sydney, it's five in the morning. The stores don't open for another five hours.” She grunts and rolls over into Dean.

  
“Hey, you.” She pokes his face. “You're going with us.” Dean grunts in protest. “Well, then I'll make sure the costumes I pick out for us are going to be slutty as can be. Hell, I might even just go right to the sex shop and buy jock straps for you two.” Dean sighs in defeat. “I'm glad you see things my way.” She smiles and crawls over to Dean and heads out the door. Cas rolls over to face Dean.

“Do you think she knew we weren't sleeping?” Dean shakes his head.

  
“She definitely knows we were spooning for a whole other reason.” He pauses for a moment. “Oh god, I hope she doesn't bring this up later.” Cas kisses him on the nose. They hear the front door close.

  
“We could always finish up what we were doing..?” Dean just grins.

 

* * *

They head through the doors of the Halloween store. Cas holds on to Dean's hand with a death grip as they follow Sydney through the store. She spots a “ **STEP HERE** ” pad on the floor and glances over her shoulder at them, their attention is drawn to a large spider hanging above their heads. She laughs to herself and she stomps on the pad causing a zombie to pop up from behind a tombstone scaring them both, resulting in Cas' nails digging into the back of Dean's hand. He glares at Sydney as she snickers at them.

  
They browse through some costumes before Cas finds the perfect one. He holds it up so they can see it. “Guys! Look! Isn't it cute?” His smile spreads from ear to ear. “And hey, I know how we can string the costumes together.” Dean pops his head up from the isle to look at the costume.

  
“Oh my goodness. You're going to look absolutely adorable in that and look what I just found.” He pulls the costume off the shelf and holds it up. “They go together like a horse and carriage.” Down the isle they hear Sydney laugh to herself. She struts to them with her costume behind her back.

  
“I've got mine and Sam's.” A devious grin on her face, she holds them both up. Cas and Dean look at each other confused. “They go together too.”

  
“Is that what Sam wants..?” Cas gets closer to get a better look at their costumes, or what's left of them. She shakes her head.

  
“Probably not, but he's outside on his phone instead of picking his out so he's getting what I choose.” Cas looks at Dean for some help with convincing her to not buy the costumes, but he only shrugs.

  
“I hate to admit it, but she does have a point. He should have come in and he wouldn't be getting stuck with this costume.” Cas frowns as he doesn't think they're being entirely fair to Sam, but knows there's no way he can prevent her from buying it. He lingers behind them as they check out and head out of the store, hoping Sam sees his costume before it's too late and he has nothing else to wear. Outside they run into him.

  
“Hey guys, I have an idea for Halloween night!” He's caught their attention now. “Why don't we head out to the woods? I heard there's a cozy cabin in the woods and we can spend the night there.” Sydney's eyes light up with excitement.

  
“Absolutely. Yes. Please. Cas?” She turns to him and he has the same expression on his face.

  
"Oh my. Yes. We have to.” Dean looks at them with his face scrunched up.

  
“We're not going to spend the night in some abandoned cabin in the woods _on Halloween_ so we can get hacked up by a chainsaw wielding maniac who just escape from the freakin' asylum. No way, not happening.” Cas looks at him with a sad look on his face. “Oh come on, don't do that to me. You're going to make me feel bad.” He sighs and rolls his eyes. “Fine. We can go to the woods on Halloween night, also known as Devil's Night because that's not a bad sign, and sleep in an abandoned cabin where we'll face our demise dressed like assholes.”

  
“Oh, hey, what costumes did you guys decide on?” None of them say anything. “I get it, it's a surprise because it's the idea I had and it's too good to spoil now. Just as long as you got mine.” Sydney nods with a smile.

 

* * *

  
**_Halloween_ **

 

Cas, Dean, and Sydney are already in their costumes as they wait for Sam to put his on. They sit in the living room of Sam's bungalow. They hear the bedroom door open and Sam walks in the room. Sydney lets out a snicker. Dean gasps. Cas tries to compliment Sam's interior design hoping to take away from the elephant in the room.

  
“Which one of you decided on Wizard of Oz characters?” Sydney and Dean point to Cas who looks uneasy. “Cas? You did this?”

  
“Well, I can assure you that my intentions weren't remotely close to this...” His eyes wander around the room trying to avoid Sam's gaze. “I wanted to be Cowardly Lion and Dean Scarecrow, Sydney would be a less provocative Dorothy and you would be Tin Man. Unfortunately, she came across the Toto outfit and they both decided this is what you would've wanted. Plus, she's pretty scary and I was afraid to disagree with her on this...though I _did_ try to reason with them or mainly Sydney.”

  
“Hey, at least you're a puppy. You would’ve been a scantily clad Dorothy instead. Ruby red slippers and all.” Dean attempts to see the bright side of this. Sam just shakes his head.

  
“Whatever, guys. Let's just get this disaster over with.” He grabs his keys and heads out the door, the other three trailing behind him. They pile into the car, Sydney forcing herself into the passenger seat leaving Cas and Dean to the backseat. It's not like she expected one of them to sit up front, she just wanted to assert her power she thought she had. The entire drive there, Sydney complains to Sam about his driving as Cas snickers in the back seat. When they finally arrive, Sam is on the verge of punching a hole in Sydney's face.

  
“Oh look there’s a few other cars here. Maybe they had the same idea we had.” Cas ogles at the other cars parked along the road. Dean sighs.

  
"Yeah, a bunch of other dumb assholes trying to get themselves abducted by aliens.” Sydney turns around in her seat, gritting her teeth and glaring at him.

  
“Shut up, Dean. Aliens are no joking matter.” Dean squints at her. They get out of the car and Dean is still glaring at Sydney trying to find out if she was being serious or not.

  
“Um..Sam, are there any flashlights?” Sam laughs and shakes his head. “How are we going to see where we're going?”

  
“You don't, that's how.” They head across the street following behind Sam. “Just make sure you stay close, guys. I don't want to lose anyone out here, there might be bears or something.”

  
“Well, Sammy, maybe if you gave us flashlights, we wouldn't need to be worrying about getting mauled by an asshole bear!” Dean grumbles. Sam just glares at him.

  
“You really use that word an awful lot, I'm beginning to think you like assholes or something.” Sam doesn't realize what he's saying before the words have come out of his mouth and Cas is doubled over laughing, on the verge of peeing his pants. Sam rolls his eyes unable to believe he actually said that.

  
“I think there are things more important than that, like the fact that there's been a mysterious silhouette darting in between the trees that none of you took notice to.” Those words send chills down their spines. Someone or _something_ was out there and it was _stalking_ them.

  
Sydney scoffs. “Come on guys, it's probably just some dumb kids playing around. It's completely harmless.” Dean shrugs.

  
“Yeah, of course. Unless, you know, _it's_ banjo playing mutant hillbillies planning to make us squeal like a bunch of pigs.” Sydney punches him in the shoulder. “ _Ow!_ You know it's probably what's out there, but like you said it's completely harmless.” She lets out a whine. “We just have to turn around and go back the way we came, no biggie. Unless we're in something like the Suicide Forest, then in that case, it was nice knowing you all.” Cas jabs him in the rib and Dean turns to face him. “Hey, what's with everyone hurting me? It's not my fault you guys wanted to come out here.” They bicker back and fourth.

  
Sam laughs at them. “At least we don't have to deal with that, ri-” He turns to Sydney, but she's no longer standing beside him. “Sydney? Stop playing around and come back.” He begins to wander around in hopes of finding her.

  
Dean turns back to where they should've been, but realizes they're both gone now. “Oh great, big dummy and little dummy have gotten themselves lost.” He grumbles.

  
“Maybe they just snuck off for a quickie..?” Cas shrugs with a smile on his face. Dean sighs knowing he's probably right.

  
“Maybe we should do the same.” He grabs Cas around the waist causing him to turn red.

  
“Do you really think that's a good idea? I mean, that thing, whatever it is could get us..” Dean looks over his shoulder and then back at Cas with a wolfish grin on his face.

  
“That's a risk I'm willing to take..” He presses a kiss to Cas' lips. “Besides, we all die sometime. Some sooner than others. At least I would die in your embrace...well with your nails and teeth embedded in my skin.” Cas rolls his eyes and Dean goes in for a kiss, but Cas pulls away. “Oh, man. I'm sorry, Cas. Am I being too pushy? I don't want to pressure you into it or an-” Cas cuts him off.

  
“No, but you do talk a lot. I can barely tell you that I'm pretty sure I see the cabin from here.” Dean lets go of him and turns around. In the distance, he can see the low lights from the cabin illuminating the surrounding shrubbery.

  
“Wanna make a bet those two went without us?” He turns back to Cas, only to notice he's already headed toward the cabin without Dean. “Hey! Don't leave me out here alone!” He jogs up to where Cas is. “Aren't you supposed to be the Cowardly Lion? I don't think he'd just waltz through the woods at night like this.”

  
“At least you're like the Scarecrow, you don't have a brain.” Cas laughs at his joke. Dean purses his lips and resists the urge to have his way with Cas and leave him in an orgasmic mess for someone else to find.

  
It isn't a far walk before they reach the cabin. Dean's hesitant about opening the door, but he has no choice once Cas is pushing him through the door and into a room full of familiar faces. They both awkwardly stand in the doorway, completely unsure what they should do next. What is one supposed to do when they run into friends in a cabin in the middle of the woods.

  
Dean turns to Cas. “Is this like a setup or something? Did Sammy set us up?” His shocked expression becomes one of annoyance.

  
“Actually, Dean, I think this is a Halloween party. I think Sam 'set us up' to have some fun.” Cas doesn't stand next to Dean much longer once he spots the candy apples. He's too distracted by the refreshments table that he doesn't notice the scheme Dean is conjuring up. Before he knows it, Dean's grabbing his hand and pulling him into a closet. Before he can protest, Dean shushes him.

  
“Hey, you're going to get your straw stuck to my apple!” Dean shushes him again. “Do not shush me while you're about to back into my Frankenstein cupcake. I will stick this apple up your ass. What are we even doing?” Dean turns around to him.

  
“We're keeping quiet, that's what we're doing.” Cas looks at him as he takes a bite of the apple. A loud crunch following after. “Okay, okay. We're going to get back at Sam and Sydney. Everyone else is hidden all over the place, except anyone dressed as a clown. When they come in and see the clowns, we'll strategically turn the lights off and they're likely to both shit their pants. Honestly, I'm hoping they do shit themselves. If you stay quiet, I'll make sure you can take the rest of the apples home, okay?” Cas looks at him as he thinks.

  
“Okay, but you better not forget the apples.” They hear the front door creak open.

 

* * *

"Did you really need to go picking at that dead deer?" The annoyance in Sam's voice reaching an all new high. Sydney just shrugs. "Now we have no clue where Cas and Dean disappeared to and we'll probably need a search and rescue team to find those two." He opens the door and allows her to go in first, following behind her only to run right into her. When he looks up he sees the clowns ominously lurking in the room. They’re both frozen in fear, unable to let out a scream or to run right back out the door they just came through.

  
After what seemed like a millennium to them, Sam grabs her arm and turns to walk out the door only to be stopped by another clown standing on the front porch. Sydney lets out a whine and as she turns back to face the room, the lights go out masking the clowns in darkness. Knowing that going out the door would result in a confrontation with the clown, they both panic. "SAMMM!!!" Sydney moves further into the room, reasons unknown, dragging Sam along by the wrist. Feeling along the wall and hoping not to encounter any other clowns, she finds a doorknob in the darkness, praying to anyone willing to listen, that it was a door back to the woods. Unfortunately for them, it feels like another room. Even more unfortunate is something touching her leg causing her to let out a scream. Sam feels around for a light and finds one. Pulling the string, he looks down. Sat on the floor of the _closet_ were a smiling Dean and a sticky Cas looking back at them.

  
“Was this your idea?! Dean, that’s not funny!” Dean laughs at them before standing up.

  
“Bravo, guys, what a show! Is there another showing?” He chuckles as he walks past them. Sam and Sydney are left staring at Cas who’s too busy enjoying his apple to notice them looking at him. When he looks up, he's confused.

  
“Cas, you were in on this?” He stands and crumbs from the cupcake fall from his lap. He brushes the excess crumbs off.

  
“Technically? Yes. Actually? No, I just sat here eating this yummy boy.” They just look at him. “Not Dean! I meant my apple..oh, he’s going to give me apples too for being quiet...that’s not synonymous with sex or anything either...Okay, I’m going to leave now before this gets even weirder.” He exits the closet and Sam looks at Sydney.

  
“They probably had to sneak away because they couldn't keep their hands off of each other.” The words come out before she can stop herself. She covers her mouth. “Oh, god.”

  
“Are they..are they like a thing or something?” She tries to get out of the situation she caused.

  
“Ha, no, no. It's just a joke because they were in a closet..” She hurries out of the closet knowing Dean is likely to kill her when he finds out.

 

 

**Notes for the Chapter:**

> Yeah, Sam is kind of getting back at them all for being shorter than them.  
> And he IS Lucifer's vessel so it makes sense that he set them up like that.  
> Anyway, I hope you're enjoying this :)


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